Water → Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamate

HRID 1092277Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][NH2:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:25](OC([O-])=O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O>ClCCl.C(N(CC)CC)C>[C:28]([O:27][C:25](=[O:26])[NH:15][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH:9]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 40 °C

Procedure

1.07 g (4 mmol, 1 eq) of [3-(5-bromopyrid-2-yl)phenyl]methylamine are dissolved in 10 mL of dichloromethane in the presence of 1 mL of triethylamine and 200 mg of dimethylaminopyridine. 1.7 g (8 mmol, 2 eq) of tert-butyl dicarbonate are added and the reaction mixture is stirred overnight at 40° C. The reaction is stopped by adding 30 ml of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.18 g of tert-butyl[3-(5-bromopyrid-2-yl)phenyl}methylcarbamate are obtained. Yield=81%.

Workup

extractionis then extracted with ethyl acetate
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-a8b9c511ae2e4f49a6dd944c3e931eab
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129416B2

Reaction notes

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